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Synthesis and fluorescence properties of 2-aryl-3-hydroxyquinolones, a new class of dyes displaying dual fluorescence
Authors:Dmytro A Yushchenko  Mykhailo D Bilokin’  Guy Duportail  Vasyl G Pivovarenko
Institution:a Department of Chemistry, Kyiv National Taras Shevchenko University, 01033 Kyiv, Ukraine
b Photophysique des Interactions Biomoléculaires, UMR 7175-LC1 du CNRS, Institut Gilbert Laustriat, Faculté de Pharmacie, Université Louis Pasteur, 67401 Illkirch, France
Abstract:A series of 2-aryl-3-hydroxyquinolones (3HQs) with different electron donating aryl substituents at the position 2 were synthesized. Their absorption and fluorescence properties were studied in solvents of medium and high polarity. Almost all the synthesized 3HQs display dual fluorescence in the tested solvents, in line with an excited state intramolecular proton transfer reaction. For N-methyl substituted compounds, the intensity ratio of the two emission bands was found to be exquisitely sensitive to solvent polarity, with a two orders of magnitude change from toluene to dimethylsulfoxide. Consequently, these compounds appear as prospective polarity fluorescent labels for proteins and nucleic acids.
Keywords:3-Hydroxyquinolones  Absorption  Fluorescence probes  Polarity sensors
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